WO2020004533A1 - Résine polythiouréthane pour élément optique et élément optique - Google Patents

Résine polythiouréthane pour élément optique et élément optique Download PDF

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Publication number
WO2020004533A1
WO2020004533A1 PCT/JP2019/025551 JP2019025551W WO2020004533A1 WO 2020004533 A1 WO2020004533 A1 WO 2020004533A1 JP 2019025551 W JP2019025551 W JP 2019025551W WO 2020004533 A1 WO2020004533 A1 WO 2020004533A1
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Prior art keywords
compound
optical member
polythiourethane resin
bis
mass
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PCT/JP2019/025551
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English (en)
Japanese (ja)
Inventor
匡人 猪狩
照夫 山下
渡邊　強
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ホヤ レンズ タイランド リミテッド
匡人 猪狩
照夫 山下
渡邊　強
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Application filed by ホヤ レンズ タイランド リミテッド, 匡人 猪狩, 照夫 山下, 渡邊　強 filed Critical ホヤ レンズ タイランド リミテッド
Priority to JP2020527620A priority Critical patent/JPWO2020004533A1/ja
Publication of WO2020004533A1 publication Critical patent/WO2020004533A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
    • C08G75/02—Polythioethers
    • C08G75/04—Polythioethers from mercapto compounds or metallic derivatives thereof
    • C08G75/045—Polythioethers from mercapto compounds or metallic derivatives thereof from mercapto compounds and unsaturated compounds
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics

Definitions

  • the present invention relates to a polythiourethane resin for an optical member and an optical member.
  • Polythiourethane resins obtained by curing a polymerizable composition containing a polyiso (thio) cyanate compound and a polythiol compound are widely used as various optical members such as lenses (for example, see Patent Document 1).
  • a resin may be dyed for imparting fashionability or light-shielding properties. If the resin constituting the optical member is inferior in dyeability, it takes a long time for the dyeing process, or it becomes difficult to impart a desired color to the optical member by the dyeing process. Therefore, the desired physical properties of the resin constituting the optical member include excellent dyeability.
  • One embodiment of the present invention provides a polythiourethane resin for an optical member having excellent dyeability.
  • the polythiourethane resin has a bond represented by the following formula 1: Is a resin having a plurality of in the molecule.
  • Z is an oxygen atom or a sulfur atom.
  • Z forms the above bond of an oxygen atom
  • the thiol group reacts with the isothiocyanate group
  • the above bond forms a sulfur atom of Z.
  • the “thiourethane bond” in the present invention and the present specification refers to a bond represented by the above formula 1.
  • * indicates the position where the thiourethane bond is bonded to another adjacent structure.
  • one embodiment of the present invention provides: A polythiourethane resin for optical members having a thiourethane bond content of 30.00% by mass or less and an ester bond content of 15.00% by mass or more (hereinafter also referred to simply as "polythiourethane resin") Described). About.
  • a polythiourethane resin for an optical member having excellent dyeability it is possible to provide a polythiourethane resin for an optical member having excellent dyeability, and an optical member obtained by dyeing the polythiourethane resin.
  • the polythiourethane resin has a thiourethane bond content of 30.00% by mass or less and an ester bond content of 15.00% by mass or more.
  • the polythiourethane resin will be described in more detail.
  • the thiourethane bond content of the polythiourethane resin is 30.00% by mass or less, preferably 25.00% by mass or less, based on the mass (100% by mass) of the polythiourethane resin. It is more preferably at most 20.00% by mass. Further, the content of the thiourethane bond is more than 0% by mass, and is 1.00% by mass or more, 2.00% by mass or more, 3.00% by mass or more, 4.00% by mass or more, % Or more, 6.00% or more, or 7.00% or more. It is preferable to lower the content of thiourethane bonds in the polythiourethane resin in order to enhance dyeability.
  • the content of the ester bond is, for example, 30.00% by mass or less or 25.00% by mass or less. It is preferable that the content of the ester bond in the polythiourethane resin is high in order to enhance the dyeability.
  • the content of thiourethane bonds and the content of ester bonds of the polythiourethane resin can be determined by a known method. Further, when the composition of the polymerizable composition for obtaining the polythiourethane resin is known, it is possible to calculate the content of thiourethane bonds and the content of ester bonds of the polythiourethane resin based on the known composition. it can. The thiourethane bond content and the ester bond content of the polythiourethane resin can be adjusted by the composition of the polymerizable composition used to obtain the polythiourethane resin.
  • the polythiourethane resin can be produced by curing a polymerizable composition. Next, the polymerizable composition that can be used to obtain the polythiourethane resin will be described in more detail.
  • the thiourethane bond can be formed by a reaction between an iso (thio) cyanate group of the polyiso (thio) cyanate compound and a thiol group of the polythiol compound (hereinafter also referred to as “thiourethane-forming reaction”). Therefore, as the polymerizable composition for obtaining the above polythiourethane resin, a polymerizable composition containing at least a polyiso (thio) cyanate compound and a polythiol compound can be used.
  • an ester bond-containing compound can be used as one or more polymerizable compounds contained in the polymerizable composition. This point will be further described later.
  • polyiso (thio) cyanate compound refers to a compound having two or more iso (thio) cyanate groups per molecule.
  • Iso (thio) cyanate means isocyanate and / or isothiocyanate. Isocyanates are sometimes called isocyanates, and isothiocyanates are sometimes called isothiocyanates.
  • Polythiol compound refers to a compound having two or more thiol groups per molecule.
  • the polyiso (thio) cyanate compound can be an aliphatic compound, an alicyclic compound, an aromatic compound, a heterocyclic compound, or the like.
  • the number of iso (thio) cyanate groups contained in the polyiso (thio) cyanate compound is 2 or more per molecule, preferably 2 to 4, more preferably 2 or 3.
  • the polyiso (thio) cyanate compound can be, for example, an aliphatic compound, an alicyclic compound, an aromatic compound, a heterocyclic compound, or the like.
  • Specific examples of the polyiso (thio) cyanate compound include hexamethylene diisocyanate, 1,5-pentane diisocyanate, isophorone diisocyanate, bis (isocyanatomethyl) cyclohexane, dicyclohexylmethane diisocyanate, and 2,5-bis (isocyanatomethyl) -bicyclo.
  • heptane 2,6-bis (isocyanatomethyl) -bicyclo
  • heptane bis (4-isocyanatocyclohexyl) methane, 1,3-bis (isocyanato) Aliphatic polyisocyanate compounds such as methyl) cyclohexane and 1,4-bis (isocyanatomethyl) cyclohexane
  • aromatic polyisocyanates such as xylylene diisocyanate, 1,3-diisocyanatobenzene, tolylene diisocyanate and diphenylmethane diisocyanate Lithocyanate compounds and the like can be mentioned.
  • the polyiso (thio) cyanate compound may be a chlorine-substituted product, a halogen-substituted product such as a bromine-substituted product, an alkyl-substituted product, an alkoxy-substituted product, a nitro-substituted product, a modified prepolymer with a polyhydric alcohol, a carbodiimide-modified product, Urea modified products, buret modified products, dimerization or trimerization reaction products, and the like can also be used.
  • a halogen-substituted product such as a bromine-substituted product, an alkyl-substituted product, an alkoxy-substituted product, a nitro-substituted product
  • a modified prepolymer with a polyhydric alcohol a carbodiimide-modified product
  • Urea modified products buret modified products, dimerization or trimerization reaction products
  • the polymerizable composition can include a cyclic structure-containing compound as the polyiso (thio) cyanate compound.
  • the cyclic structure-containing compound may be a carbocyclic compound, a heterocyclic compound, a monocyclic compound, or a bicyclic or higher polycyclic compound.
  • the polyiso (thio) cyanate compound may include a plurality of cyclic structures.
  • the polyiso (thio) cyanate compound can be an aromatic compound (aromatic polyiso (thio) cyanate compound).
  • the polyiso (thio) cyanate compound can be an ester bond-containing compound.
  • the polyiso (thio) cyanate compound containing an ester bond can contain, for example, two or more ester bonds per molecule, for example, two to five ester bonds.
  • the content of the polyiso (thio) cyanate compound in the polymerizable composition is, for example, more than 0% by mass and 50.00% by mass or less, preferably 10.00% by mass, based on the mass (100% by mass) of the polymerizable composition. It can be in the range of ⁇ 35.00% by mass.
  • the mass of the polymerizable composition means the mass excluding the solvent when the polymerizable composition contains a solvent.
  • the polythiol compound can be an aliphatic compound, an alicyclic compound, an aromatic compound, a heterocyclic compound, or the like.
  • the number of thiol groups contained in the polythiol compound is two or more per molecule, preferably 2 to 4. Further, the number of thiol groups contained in the polythiol compound is preferably 3 or more per molecule.
  • polythiol compound examples include methanedithiol, 1,2-ethanedithiol, 1,1-propanedithiol, 1,2-propanedithiol, 1,3-propanedithiol, 2,2-propanedithiol, and 1,6-hexane Dithiol, 1,2,3-propanetrithiol, tetrakis (mercaptomethyl) methane, 1,1-cyclohexanedithiol, 1,2-cyclohexanedithiol, 2,2-dimethylpropane-1,3-dithiol, 3,4- Dimethoxybutane-1,2-dithiol, 2-methylcyclohexane-2,3-dithiol, 1,1-bis (mercaptomethyl) cyclohexane, bis (2-mercaptoethyl thiomalate), 2,3-dimercaptosuccinic acid (2-mercaptoethyl ester), 2,3 Dimer
  • Polythiol compounds containing a sulfur atom in addition to a thiol group such as one of the isomers or a mixture of two or three of these isomers); 3,4-thiophenedithiol, tetrahydrothiophene-2,5-dimercaptomethyl Containing a sulfur atom in addition to thiol groups such as 2,5-dimercapto-1,3,4-thiadiazole, 2,5-dimercapto-1,4-dithiane and 2,5-dimercaptomethyl-1,4-dithiane And the like.
  • the polythiol compound contained in the polymerizable composition can be an aliphatic compound.
  • the polythiol compound can be an ester bond-containing compound.
  • the polythiol compound containing an ester bond can contain, for example, two or more ester bonds per molecule, for example, 2 to 5 ester bonds.
  • the polythiol compound in one aspect, can be an ester bond-containing aliphatic compound.
  • the content of the polythiol compound in the polymerizable composition is, for example, 20.00 to 80.00% by mass, preferably 30.00 to 70.00% by mass with respect to the mass (100% by mass) of the polymerizable composition. %.
  • the polymerizable composition may include one or more other polymerizable compounds in addition to the polyiso (thio) cyanate compound and the polythiol compound.
  • examples of such a polymerizable compound include a polyene compound.
  • polyene compound refers to a compound having two or more carbon-carbon double bonds per molecule.
  • a cured product of the polymerizable composition containing a polyene compound and a polythiol compound reacts with a carbon-carbon double bond of the polyene compound and a thiol group of the polythiol compound (hereinafter referred to as a “thiol-ene reaction”).
  • the number of carbon-carbon double bonds of the polyene compound is 2 or more, preferably 3 or more, for example, 3 to 5 per molecule.
  • the polyene compound can include a carbon-carbon double bond in a carbon-carbon double bond-containing group such as a (meth) acryl group, a vinyl group, and an allyl group.
  • the types of the carbon-carbon double bond-containing groups contained in the polyene compound may be the same or different.
  • polyene compound examples include vinyl compounds such as divinylbenzene and divinyltoluene, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, and trimethylolpropane tri (meth) acrylate.
  • (Meth) acrylates such as trimethylolpropane di (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, tetraethylene glycol di (meth) acrylate, and isocyanuric acid ethylene oxide-modified tri (meth) acrylate , Diallyl phthalate, diallyl maleate, triallyl cyanurate, triallyl isocyanurate, triallyl trimellitate, tetraallyl Allyl compounds such as Kishietan like.
  • the polyene compound only one kind of polyene compound may be used, or two or more kinds may be used as a mixture.
  • the polyene compound can be, for example, an aliphatic compound, an alicyclic compound, an aromatic compound, a heterocyclic compound, or the like.
  • the polyene compound can be a cyclic structure containing compound.
  • the cyclic structure-containing compound may be a carbocyclic compound, a heterocyclic compound, a monocyclic compound, or a bicyclic or higher polycyclic compound. Good.
  • the polyene compound may include a plurality of cyclic structures.
  • the polyene compound can be a heteroalicyclic or heteroaromatic compound, and specifically can be an isocyanuric ring-containing compound or a cyanuric ring-containing compound.
  • the polyene compound can be an ester bond-containing compound.
  • the polyene compound containing an ester bond can contain, for example, two or more ester bonds per molecule, for example, two to five ester bonds.
  • the content of the polyene compound in the polymerizable composition is, for example, more than 0% by mass and 50.00% by mass or less, preferably 10.00 to 35.00, based on the mass (100% by mass) of the polymerizable composition. % By weight.
  • the polymerizable composition may optionally contain one or more known components such as additives and polymerization catalysts generally used for the production of optical members.
  • the additive include various additives such as an ultraviolet absorber, an antioxidant, and a release agent.
  • an organic phosphorus compound such as a phosphine derivative can be used as an additive. The amount of the additive used can be appropriately set.
  • the polymerizable composition includes, as a polymerization catalyst, a polymerization catalyst that catalyzes a thiourethanation reaction between a polyiso (thio) cyanate compound and a polythiol compound (hereinafter, also referred to as “first polymerization catalyst”). Is preferred.
  • a polymerization catalyst that catalyzes a thiol-ene reaction between the polyene compound and the polyiso (thio) cyanate compound hereinafter also referred to as a “second polymerization catalyst” Is preferably used in combination with the first polymerization catalyst.
  • first polymerization catalyst that catalyzes the thiourethane reaction As the first polymerization catalyst that catalyzes the thiourethane reaction and the second polymerization catalyst that catalyzes the thiol-ene reaction, known polymerization catalysts can be used.
  • the first polymerization catalyst that catalyzes the thiourethanation reaction include dibutyltin diacetate, dibutyltin dilaurate, dibutyltin dichloride, dimethyltin dichloride, monomethyltin trichloride, trimethyltin chloride, tributyltin chloride, and tributyltin.
  • Organic tin compounds such as fluoride and dimethyltin dibromide can be mentioned.
  • the polymerizable composition can contain, for example, the first polymerization catalyst in an amount of 0.01 to 0.50% by mass based on the mass (100% by mass) of the polymerizable composition.
  • the second polymerization catalyst that catalyzes the thiol-ene reaction include 2,2′-azobisisobutyronitrile, 2,2′-azobis (2-methylbutyronitrile), and 2,2′-azobis-2.
  • the polymerizable composition can be prepared by mixing the various components described above simultaneously or sequentially in an arbitrary order.
  • the preparation method is not particularly limited, and a known method for preparing a polymerizable composition can be employed. Further, the polymerizable composition may be prepared without adding a solvent, or may be prepared by adding an arbitrary amount of a solvent. As the solvent, one or more known solvents that can be used for the polymerizable composition can be used.
  • the polyiso (thio) cyanate compound, polythiol compound, and polyene compound described above are all polymerizable compounds, and the above polymerizable composition is cured by polymerizing these compounds to obtain a cured product (polythiourethane resin). ) Can be obtained.
  • the polythiourethane resin thus obtained can be used as various optical members.
  • the optical member include various lenses such as a spectacle lens, a telescope lens, a binocular lens, a microscope lens, an endoscope lens, and an imaging system lens of various cameras.
  • the “lens” in the present invention and the present specification includes a “lens substrate” in which one or more layers are arbitrarily laminated.
  • cast polymerization is preferable.
  • the polymerizable composition is injected into a cavity of a mold having two cavities facing each other at a predetermined interval and a cavity formed by closing the space, and the polymerizable composition is injected into the cavity.
  • the polymerization (curing reaction) of the polymerizable compound contained in the above can be performed to obtain a cured product.
  • molds usable for casting polymerization refer to, for example, paragraphs 0012 to 0014 of JP-A-2009-262480 and FIG. 1 of the same.
  • a molding die in which a gap between two molds is closed by a gasket as a sealing member is shown, but a tape may be used as the sealing member.
  • the casting polymerization can be performed as follows.
  • the polymerizable composition is injected into the mold cavity from an injection port provided on the side surface of the mold.
  • the polymerizable compound contained in the polymerizable composition is preferably polymerized (cured reaction) by heating, whereby the polymerizable composition is cured, and a cured product in which the internal shape of the cavity is transferred can be obtained.
  • the polymerization conditions are not particularly limited, and can be appropriately set according to the composition of the polymerizable composition and the like.
  • the mold in which the polymerizable composition has been injected into the cavity can be heated at a heating temperature of 20 to 150 ° C.
  • the temperature such as a heating temperature for casting polymerization refers to an ambient temperature at which a mold is placed.
  • the temperature can be increased at an arbitrary rate, and the temperature can be decreased (cooled) at an arbitrary rate.
  • the cured product inside the cavity is released from the mold.
  • the cured product can be released from the mold by removing the upper and lower molds and the gasket or tape forming the cavity in any order.
  • the cured product (polythiourethane resin) released from the mold can be used as an optical member after post-processing as necessary, and can be used as, for example, various lenses (for example, a lens substrate).
  • a cured product used as a lens base material for an eyeglass lens is usually, after release, annealing, dyeing, a grinding process such as a rounding process, a polishing process, a primer coat layer for improving impact resistance, and a surface. It can be applied to a post-process such as a process of forming a coat layer such as a hard coat layer for increasing hardness.
  • various functional layers such as an antireflection layer and a water-repellent layer can be formed on the lens substrate. For each of these steps, a known technique can be applied.
  • an eyeglass lens in which the lens substrate is the above polythiourethane resin can be obtained.
  • spectacles can be obtained by attaching this spectacle lens to a frame.
  • the above polythiourethane resin can be preferably subjected to a dyeing treatment.
  • the polythiourethane resin can exhibit excellent dyeability.
  • the dyeing treatment can be performed, for example, by immersing the cured product in a dyeing bath containing a dye.
  • the dyeing bath can be prepared, for example, by diluting a commercially available dye with a solvent as necessary.
  • known additives such as a surfactant can be added to the dyeing bath as needed.
  • the temperature of the dye bath can be, for example, in the range from 30 to 100 ° C.
  • the immersion time of the cured product in the dyeing bath is not particularly limited, but is, for example, about 1 minute to 1 hour.
  • a heat treatment may be performed to fix the dye.
  • the heating temperature in this heat treatment (for example, the ambient temperature in the furnace of the heating furnace for performing the heat treatment) is, for example, 30 ° C. to 120 ° C., and the heat treatment time is, for example, 15 minutes to 2 hours, but is not particularly limited.
  • washing and one or more of the post-processes exemplified above can be performed.
  • One embodiment of the present invention relates to an optical member obtained by dyeing the polythiourethane resin.
  • the above description can be referred to for details regarding the above-mentioned polythiourethane resin and optical members such as dyeing treatment.
  • PETMA pentaerythritol tetrakis (2-mercaptoacetate)
  • a plastic lens having a center thickness of 2 mm was produced.
  • the plastic lens thus produced has a thiourethane bond content of 38.42% by mass and an ester bond content of 22.54% by mass.
  • Example 1 A 300 ml eggplant-shaped flask was charged with 10.9 g of 2,4-tolylene diisocyanate (TDI) as a polyiso (thio) cyanate compound and 32.8 g of triallyl isocyanurate (TAIC) as a polyene compound, and triphenylphosphine as an organic phosphorus compound.
  • TDI 2,4-tolylene diisocyanate
  • TAIC triallyl isocyanurate
  • triphenylphosphine an organic phosphorus compound.
  • TPP butoxyethyl acid phosphate
  • JP-506H butoxyethyl acid phosphate
  • dimethyltin dichloride 0.01 g
  • 2,2′-azobis-2,4-dimethyl 0.02 g of valeronitrile was added, and stirring was continued for 1 hour under a nitrogen purge at 20 ° C.
  • PETMA pentaerythritol tetrakis (2-mercaptoacetate)
  • a plastic lens having a center thickness of 2 mm was produced.
  • the plastic lens thus manufactured has a thiourethane bond content of 9.41% by mass and an ester bond content of 22.89% by mass.
  • Example 2 In a 300 ml eggplant-shaped flask, 22.0 g of 2,4-tolylene diisocyanate (TDI) as a polyiso (thio) cyanate compound and 22.0 g of triallyl isocyanurate (TAIC) as a polyene compound were charged, and triphenylphosphine was used as an organic phosphorus compound.
  • TDI 2,4-tolylene diisocyanate
  • TAIC triallyl isocyanurate
  • TPP butoxyethyl acid phosphate
  • JP-506H butoxyethyl acid phosphate
  • dimethyltin dichloride 0.02 g
  • 2,2′-azobis-2,4-dimethyl 0.02 g of valeronitrile was added, and stirring was continued for 1 hour under a nitrogen purge at 20 ° C.
  • PETMA pentaerythritol tetrakis (2-mercaptoacetate)
  • a plastic lens having a center thickness of 2 mm was produced.
  • the plastic lens thus manufactured has a thiourethane bond content of 18.98% by mass and an ester bond content of 22.78% by mass.
  • Example 3 A 300 ml eggplant-shaped flask was charged with 33.2 g of 2,4-tolylene diisocyanate (TDI) as a polyiso (thio) cyanate compound and 11.1 g of triallyl isocyanurate (TAIC) as a polyene compound, and triphenylphosphine as an organic phosphorus compound.
  • TDI 2,4-tolylene diisocyanate
  • TAIC triallyl isocyanurate
  • triphenylphosphine an organic phosphorus compound.
  • TPP butoxyethyl acid phosphate
  • JP-506H manufactured by Johoku Chemical Co., Ltd.
  • dimethyltin dichloride 0.03 g
  • 2,2′-azobis-2,4-dimethyl 0.02 g of valeronitrile was added, and stirring was continued for 1 hour under a nitrogen purge at 20 ° C.
  • PETMA pentaerythritol tetrakis (2-mercaptoacetate)
  • a plastic lens having a center thickness of 2 mm was produced.
  • the plastic lens thus produced has a thiourethane bond content of 28.74% by mass and an ester bond content of 22.66% by mass.
  • Each of the plastic lenses of Examples 1 to 3 and the plastic lens of Comparative Example 1 is a polythiourethane resin prepared from a polymerizable composition containing a polyiso (thio) cyanate compound and a polythiol compound.
  • the plastic lenses of Examples 1 to 3 having a content of 30.00% by mass or less and an ester bond content of 15.00% by mass or more had better dyeability (higher dyeing density) than the plastic lens of Comparative Example 1. )showed that.
  • Such plastic lenses of Examples 1 to 3 are suitable as various optical members such as spectacle lenses which are desired to have excellent dyeability.
  • the polymerizable compositions 1 to 4 contain various polymerizable compounds in a molar ratio such that the total amount of the isocyanate groups of the polyiso (thio) cyanate compound can react with the thiol groups contained in the polythiol compound.
  • the thiourethane bond content is a value calculated by the following formula, assuming that all the isocyanate groups of the polyiso (thio) cyanate compound react to form a thiourethane bond.
  • Thiourethane bond content (mass of thiourethane bond formed / total weight of polymerizable composition) ⁇ 100
  • PETMA which is a polythiol compound contained in the polymerizable compositions 1 to 4, contains an ester bond.
  • a polythiourethane resin for an optical member having a thiourethane bond content of 30.00% by mass or less and an ester bond content of 15.00% by mass or more.
  • the polythiourethane resin can exhibit high dyeability.
  • the content of the ester bond in the polythiourethane resin can be in the range of 15.00 to 30.00% by mass.
  • the polythiourethane resin can be a cured product obtained by curing a polymerizable composition containing a polyene compound, a polyiso (thio) cyanate compound, and a polythiol compound.
  • the polyene compound may be a cyclic structure-containing compound.
  • the cyclic structure can be an isocyanuric ring.
  • the polyene compound can be an allyl compound.
  • the polyene compound may be a compound containing three or more carbon-carbon double bonds per molecule.
  • the polythiol compound can be an aliphatic compound.
  • the polythiol compound can be an ester bond-containing compound.
  • the polythiol compound may be a compound containing three or more thiol groups per molecule.
  • the polyiso (thio) cyanate compound can be an aromatic compound.
  • the optical member may be a lens.
  • the lens may be a spectacle lens.
  • an optical member obtained by dyeing the polythiourethane resin.
  • One embodiment of the present invention is useful in the field of manufacturing various optical members such as spectacle lenses.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Eyeglasses (AREA)
  • Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)

Abstract

Une résine polythiouréthane pour un élément optique contenant 30,00 % en masse ou moins d'une liaison thiouréthane et 15,00 % en masse ou plus d'une liaison ester.
PCT/JP2019/025551 2018-06-29 2019-06-27 Résine polythiouréthane pour élément optique et élément optique WO2020004533A1 (fr)

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JPWO2020004531A1 (ja) * 2018-06-29 2021-07-08 ホヤ レンズ タイランド リミテッドＨＯＹＡ Ｌｅｎｓ Ｔｈａｉｌａｎｄ Ｌｔｄ 光学部材用重合性組成物、光学部材および光学部材の製造方法

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